CA2281745A1 - Method for carrying out polycondensation reactions - Google Patents
Method for carrying out polycondensation reactions Download PDFInfo
- Publication number
- CA2281745A1 CA2281745A1 CA002281745A CA2281745A CA2281745A1 CA 2281745 A1 CA2281745 A1 CA 2281745A1 CA 002281745 A CA002281745 A CA 002281745A CA 2281745 A CA2281745 A CA 2281745A CA 2281745 A1 CA2281745 A1 CA 2281745A1
- Authority
- CA
- Canada
- Prior art keywords
- reactor
- bar
- reaction
- viscosity
- acid
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Abandoned
Links
- 238000000034 method Methods 0.000 title claims abstract description 32
- 238000006068 polycondensation reaction Methods 0.000 title claims abstract description 28
- 239000000047 product Substances 0.000 claims abstract description 40
- 238000001704 evaporation Methods 0.000 claims abstract description 13
- 230000008020 evaporation Effects 0.000 claims abstract description 13
- 239000007795 chemical reaction product Substances 0.000 claims abstract description 4
- 238000006243 chemical reaction Methods 0.000 claims description 35
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 28
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 24
- 239000002253 acid Substances 0.000 claims description 20
- 239000011541 reaction mixture Substances 0.000 claims description 16
- 239000007858 starting material Substances 0.000 claims description 15
- 238000004898 kneading Methods 0.000 claims description 12
- 230000008030 elimination Effects 0.000 claims description 11
- 238000003379 elimination reaction Methods 0.000 claims description 11
- 229920000642 polymer Polymers 0.000 claims description 11
- 229910021529 ammonia Inorganic materials 0.000 claims description 10
- 150000003863 ammonium salts Chemical class 0.000 claims description 10
- 239000007787 solid Substances 0.000 claims description 9
- 239000007864 aqueous solution Substances 0.000 claims description 6
- 230000007062 hydrolysis Effects 0.000 claims description 6
- 238000006460 hydrolysis reaction Methods 0.000 claims description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims description 4
- CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 4
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 4
- 239000000203 mixture Substances 0.000 claims description 3
- 239000002245 particle Substances 0.000 claims description 3
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 claims description 2
- HSBSUGYTMJWPAX-UHFFFAOYSA-N 2-hexenedioic acid Chemical compound OC(=O)CCC=CC(O)=O HSBSUGYTMJWPAX-UHFFFAOYSA-N 0.000 claims description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 claims description 2
- 235000011037 adipic acid Nutrition 0.000 claims description 2
- 229960000250 adipic acid Drugs 0.000 claims description 2
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 claims description 2
- 235000003704 aspartic acid Nutrition 0.000 claims description 2
- OQFSQFPPLPISGP-UHFFFAOYSA-N beta-carboxyaspartic acid Natural products OC(=O)C(N)C(C(O)=O)C(O)=O OQFSQFPPLPISGP-UHFFFAOYSA-N 0.000 claims description 2
- 239000001530 fumaric acid Substances 0.000 claims description 2
- 235000011087 fumaric acid Nutrition 0.000 claims description 2
- 239000011346 highly viscous material Substances 0.000 claims description 2
- 230000002401 inhibitory effect Effects 0.000 claims description 2
- 239000010954 inorganic particle Substances 0.000 claims description 2
- 239000001630 malic acid Substances 0.000 claims description 2
- 235000011090 malic acid Nutrition 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 239000011146 organic particle Substances 0.000 claims description 2
- 239000002244 precipitate Substances 0.000 claims description 2
- 238000010008 shearing Methods 0.000 claims description 2
- 238000003797 solvolysis reaction Methods 0.000 claims description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims 2
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims 2
- 239000011976 maleic acid Substances 0.000 claims 2
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 claims 1
- 238000003776 cleavage reaction Methods 0.000 abstract 1
- 230000007017 scission Effects 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 46
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 27
- 238000012360 testing method Methods 0.000 description 19
- XLOMVQKBTHCTTD-UHFFFAOYSA-N zinc oxide Inorganic materials [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 11
- 238000002360 preparation method Methods 0.000 description 10
- 239000002904 solvent Substances 0.000 description 10
- 229920000805 Polyaspartic acid Polymers 0.000 description 9
- 238000002156 mixing Methods 0.000 description 9
- 108010064470 polyaspartate Proteins 0.000 description 9
- 238000009833 condensation Methods 0.000 description 8
- 230000005494 condensation Effects 0.000 description 8
- 239000000126 substance Substances 0.000 description 8
- 239000011550 stock solution Substances 0.000 description 7
- 239000003112 inhibitor Substances 0.000 description 6
- RPACBEVZENYWOL-XFULWGLBSA-M sodium;(2r)-2-[6-(4-chlorophenoxy)hexyl]oxirane-2-carboxylate Chemical compound [Na+].C=1C=C(Cl)C=CC=1OCCCCCC[C@]1(C(=O)[O-])CO1 RPACBEVZENYWOL-XFULWGLBSA-M 0.000 description 6
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 150000008064 anhydrides Chemical class 0.000 description 5
- 229960005069 calcium Drugs 0.000 description 5
- 239000011575 calcium Substances 0.000 description 5
- 229910052791 calcium Inorganic materials 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 241000196324 Embryophyta Species 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical class OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- 239000006185 dispersion Substances 0.000 description 4
- 239000000178 monomer Substances 0.000 description 4
- 238000012545 processing Methods 0.000 description 4
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 3
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 3
- 108010009736 Protein Hydrolysates Proteins 0.000 description 3
- 235000011114 ammonium hydroxide Nutrition 0.000 description 3
- 239000012153 distilled water Substances 0.000 description 3
- 238000009826 distribution Methods 0.000 description 3
- 238000007429 general method Methods 0.000 description 3
- -1 hydrogen halides Chemical class 0.000 description 3
- 230000005764 inhibitory process Effects 0.000 description 3
- 239000003531 protein hydrolysate Substances 0.000 description 3
- 238000012546 transfer Methods 0.000 description 3
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical class NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
- 239000004697 Polyetherimide Substances 0.000 description 2
- 239000004642 Polyimide Substances 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical class OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 238000001125 extrusion Methods 0.000 description 2
- 230000009969 flowable effect Effects 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 229920002521 macromolecule Polymers 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000012528 membrane Substances 0.000 description 2
- 229920000728 polyester Polymers 0.000 description 2
- 229920001601 polyetherimide Polymers 0.000 description 2
- 229920000139 polyethylene terephthalate Polymers 0.000 description 2
- 239000005020 polyethylene terephthalate Substances 0.000 description 2
- 229920001721 polyimide Polymers 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000004448 titration Methods 0.000 description 2
- WWILHZQYNPQALT-UHFFFAOYSA-N 2-methyl-2-morpholin-4-ylpropanal Chemical compound O=CC(C)(C)N1CCOCC1 WWILHZQYNPQALT-UHFFFAOYSA-N 0.000 description 1
- DCXYFEDJOCDNAF-UHFFFAOYSA-N Asparagine Natural products OC(=O)C(N)CC(N)=O DCXYFEDJOCDNAF-UHFFFAOYSA-N 0.000 description 1
- 101100352919 Caenorhabditis elegans ppm-2 gene Proteins 0.000 description 1
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical class NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 1
- 229920001634 Copolyester Polymers 0.000 description 1
- DCXYFEDJOCDNAF-REOHCLBHSA-N L-asparagine Chemical compound OC(=O)[C@@H](N)CC(N)=O DCXYFEDJOCDNAF-REOHCLBHSA-N 0.000 description 1
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical class OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 1
- 108010073771 Soybean Proteins Proteins 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 240000008042 Zea mays Species 0.000 description 1
- 235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 description 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 150000001414 amino alcohols Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 235000009582 asparagine Nutrition 0.000 description 1
- 229960001230 asparagine Drugs 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- LLSDKQJKOVVTOJ-UHFFFAOYSA-L calcium chloride dihydrate Chemical compound O.O.[Cl-].[Cl-].[Ca+2] LLSDKQJKOVVTOJ-UHFFFAOYSA-L 0.000 description 1
- 229940052299 calcium chloride dihydrate Drugs 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 235000014633 carbohydrates Nutrition 0.000 description 1
- 150000001720 carbohydrates Chemical class 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000011552 falling film Substances 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 239000010408 film Substances 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 150000002337 glycosamines Chemical class 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 238000003402 intramolecular cyclocondensation reaction Methods 0.000 description 1
- 229940050906 magnesium chloride hexahydrate Drugs 0.000 description 1
- DHRRIBDTHFBPNG-UHFFFAOYSA-L magnesium dichloride hexahydrate Chemical compound O.O.O.O.O.O.[Mg+2].[Cl-].[Cl-] DHRRIBDTHFBPNG-UHFFFAOYSA-L 0.000 description 1
- 235000009973 maize Nutrition 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 238000011020 pilot scale process Methods 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 229920001748 polybutylene Polymers 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 229920000137 polyphosphoric acid Chemical class 0.000 description 1
- CHKVPAROMQMJNQ-UHFFFAOYSA-M potassium bisulfate Chemical compound [K+].OS([O-])(=O)=O CHKVPAROMQMJNQ-UHFFFAOYSA-M 0.000 description 1
- 229910000343 potassium bisulfate Inorganic materials 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- WBHQBSYUUJJSRZ-UHFFFAOYSA-M sodium bisulfate Chemical compound [Na+].OS([O-])(=O)=O WBHQBSYUUJJSRZ-UHFFFAOYSA-M 0.000 description 1
- 229910000342 sodium bisulfate Inorganic materials 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000007962 solid dispersion Substances 0.000 description 1
- 229940001941 soy protein Drugs 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- IIACRCGMVDHOTQ-UHFFFAOYSA-N sulfamic acid Chemical class NS(O)(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-N 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- KKEYFWRCBNTPAC-UHFFFAOYSA-L terephthalate(2-) Chemical compound [O-]C(=O)C1=CC=C(C([O-])=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-L 0.000 description 1
- ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical class C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
- C08G73/0605—Polycondensates containing five-membered rings, not condensed with other rings, with nitrogen atoms as the only ring hetero atoms
- C08G73/0611—Polycondensates containing five-membered rings, not condensed with other rings, with nitrogen atoms as the only ring hetero atoms with only one nitrogen atom in the ring, e.g. polypyrroles
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G69/00—Macromolecular compounds obtained by reactions forming a carboxylic amide link in the main chain of the macromolecule
- C08G69/02—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids
- C08G69/04—Preparatory processes
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Polyamides (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
- Polyesters Or Polycarbonates (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19706901A DE19706901A1 (de) | 1997-02-21 | 1997-02-21 | Verfahren zur Durchführung von Polykondensationsreaktionen |
| DE19706901.0 | 1997-02-21 | ||
| PCT/EP1998/000740 WO1998037123A1 (de) | 1997-02-21 | 1998-02-10 | Verfahren zur durchführung von polykondensationsreaktionen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2281745A1 true CA2281745A1 (en) | 1998-08-27 |
Family
ID=7821050
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002281745A Abandoned CA2281745A1 (en) | 1997-02-21 | 1998-02-10 | Method for carrying out polycondensation reactions |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US6187898B1 (ja) |
| EP (1) | EP0963396B1 (ja) |
| JP (1) | JP2001509207A (ja) |
| KR (1) | KR20000075492A (ja) |
| AU (1) | AU6396998A (ja) |
| CA (1) | CA2281745A1 (ja) |
| DE (2) | DE19706901A1 (ja) |
| ES (1) | ES2182281T3 (ja) |
| WO (1) | WO1998037123A1 (ja) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2001044150A2 (en) * | 1999-12-17 | 2001-06-21 | E.I. Du Pont De Nemours And Company | Continuous process for the preparation of polytrimethylene ether glycol |
| US20040249114A1 (en) * | 2001-02-06 | 2004-12-09 | Graham Swift | Methods of synthesis of polysuccinimide or polyaspartate by end capping polymerization |
| US20060211843A1 (en) * | 2001-02-06 | 2006-09-21 | Graham Swift | Methods of synthesis of poly(succinimide-aspartate) polysuccinimide or polyaspartate by end capping polymerization |
| US7074881B2 (en) * | 2001-02-06 | 2006-07-11 | Folia, Inc | Methods of synthesis of polysuccinimide, copolymers of polysuccinimide and derivatives thereof |
| US20040249115A1 (en) * | 2001-02-06 | 2004-12-09 | Graham Swift | Methods of synthesis of poly(succinimide-aspartate) copolymer by end-capping polymerization |
| DE10124903A1 (de) | 2001-05-22 | 2002-11-28 | Bayer Ag | Thixotrope Dispersionen von Polysuccinimid und deren Anwendung |
| US20060205919A1 (en) * | 2005-03-09 | 2006-09-14 | Graham Swift | Derivatives of end capped polysuccinimides |
| EP3088682B1 (en) * | 2015-04-29 | 2017-11-22 | General Electric Technology GmbH | Control concept for closed brayton cycle |
| WO2018035337A1 (en) | 2016-08-18 | 2018-02-22 | Eastman Chemical Company | Polyester compositions which comprise tetramethylcyclobutandiol and ethylene glycol, with improved catalyst system |
| WO2018035345A1 (en) | 2016-08-18 | 2018-02-22 | Eastman Chemical Company | Oriented films and shrink films comprising polyesters which comprise tetramethyl cyclobutanediol and ethylene glycol |
| JP7130621B2 (ja) | 2016-08-18 | 2022-09-05 | イーストマン ケミカル カンパニー | 改良された触媒系による、テトラメチルシクロブタンジオール及びエチレングリコールを含むポリエステル組成物 |
Family Cites Families (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4313870B1 (en) * | 1977-09-21 | 1996-06-18 | Sumitomo Chemical Co | Process for producing polycondensates |
| US4603193A (en) * | 1983-02-16 | 1986-07-29 | Amoco Corporation | Polycondensation process with aerosol mist of aqueous solution of reactant salts |
| US5221733A (en) * | 1991-02-22 | 1993-06-22 | Donlar Corporation | Manufacture of polyaspartic acids |
| US5288783A (en) * | 1992-05-14 | 1994-02-22 | Srchem Incorporated | Preparation of salt of polyaspartic acid by high temperature reaction |
| CH684893A5 (de) * | 1992-09-09 | 1995-01-31 | Inventa Ag | Verfahren zur Herstellung von amorphen teilaromatischen hochmolekularen Copolyamiden. |
| US5219952A (en) * | 1992-09-18 | 1993-06-15 | Donlar Corporation | Production of high molecular weight polysuccinimide and high molecular weight polyaspartic acid from maleic anhydride and ammonia |
| DE4244031A1 (de) * | 1992-12-24 | 1994-06-30 | Bayer Ag | Verfahren zur Herstellung und Verwendung von Polyasparaginsäure und ihrer Salze |
| DE4300020A1 (de) * | 1993-01-02 | 1994-07-07 | Basf Ag | Verfahren zur Herstellung von Polymerisaten der Asparaginsäure und ihre Verwendung |
| DE4319044A1 (de) * | 1993-05-06 | 1994-11-10 | Bayer Ag | Verfahren zur Herstellung von Polysuccinimid und Polyasparaginsäure |
| DE4425951A1 (de) * | 1994-07-21 | 1996-01-25 | Bayer Ag | Verfahren zur Herstellung von Asparaginsäure-haltigen Polymeren |
| DE4337337C2 (de) * | 1993-11-02 | 1999-04-15 | Bayer Ag | Verfahren zur Herstellung von Polysuccinimid |
| DE59409048D1 (de) * | 1993-11-02 | 2000-02-10 | Bayer Ag | Verfahren zur Herstellung von Asparaginsäure-haltigen Polymeren |
| US5493004A (en) * | 1994-04-08 | 1996-02-20 | Bayer Ag | Process for the preparation of polysuccinimide |
| DE4427233A1 (de) * | 1994-06-29 | 1996-01-04 | Basf Ag | Verfahren zur Herstellung von Polyasparaginsäure und/oder Polyasparaginsäureimiden |
| DE4425952A1 (de) * | 1994-07-21 | 1996-01-25 | Bayer Ag | Verfahren zur Herstellung von Polysuccinimid oder Maleinamidsäure |
| DE4429108A1 (de) * | 1994-08-17 | 1996-02-22 | Basf Ag | Verfahren zur Polykondensation von Ammoniakderivaten der Asparaginsäure |
| DE19612139A1 (de) * | 1996-03-27 | 1997-10-02 | Bayer Ag | Zweistufenverfahren zur Herstellung von thermoplastischem Polycarbonat |
-
1997
- 1997-02-21 DE DE19706901A patent/DE19706901A1/de not_active Withdrawn
-
1998
- 1998-02-10 US US09/367,457 patent/US6187898B1/en not_active Expired - Lifetime
- 1998-02-10 KR KR1019997007551A patent/KR20000075492A/ko not_active Application Discontinuation
- 1998-02-10 JP JP53621898A patent/JP2001509207A/ja active Pending
- 1998-02-10 WO PCT/EP1998/000740 patent/WO1998037123A1/de not_active Application Discontinuation
- 1998-02-10 CA CA002281745A patent/CA2281745A1/en not_active Abandoned
- 1998-02-10 EP EP98909435A patent/EP0963396B1/de not_active Expired - Lifetime
- 1998-02-10 DE DE59806114T patent/DE59806114D1/de not_active Expired - Lifetime
- 1998-02-10 ES ES98909435T patent/ES2182281T3/es not_active Expired - Lifetime
- 1998-02-10 AU AU63969/98A patent/AU6396998A/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| JP2001509207A (ja) | 2001-07-10 |
| EP0963396A1 (de) | 1999-12-15 |
| US6187898B1 (en) | 2001-02-13 |
| WO1998037123A1 (de) | 1998-08-27 |
| ES2182281T3 (es) | 2003-03-01 |
| DE59806114D1 (de) | 2002-12-05 |
| DE19706901A1 (de) | 1998-08-27 |
| EP0963396B1 (de) | 2002-10-30 |
| AU6396998A (en) | 1998-09-09 |
| KR20000075492A (ko) | 2000-12-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Discontinued |